2. Craig Smith, Dallas Stars
When Craig Smith inked a three-year, $9.3 million contract with the Bruins in October 2020, he was expected to contribute as a top six forward. He came to Boston from the Nashville Predators having reached the 20 goal plateau in five of his last seven seasons. Unfortunately, Smith failed to reach those expectations, and never topped 16 goals in any of his two and a half seasons with the Bruins.
Smith's contract was considered an albatross during last season's historic regular season, as Boston looked to upgrade for a playoff run but needed to offload Smith's contract and undesirable play (four goals in 42 games for Boston) to make room for incoming reinforcements.
Ultimately, the Bruins were able to ship him to Washington as part of a three-team trade that allowed Boston to acquire forward Garnet Hathaway and defenseman Dmitry Orlov. Boston packaged extensive draft capital with Smith to part ways, attaching a 2023 first-round pick, a 2025 second-round pick and a 2024 third-round pick in addition to the winger.
After finishing the 2022-23 season in Washington, Smith signed with the Dallas Stars in free agency on a one-year, $1 million contract. In a much diminished role, he has only recorded three points through 24 games this season. Every Boston skater with at least 20 games played has registered more points.
Smith's contract and time in Boston will go down as a swing and a miss.